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Clickable azide-functionalized bromoarylaldehydes - synthesis and photophysical characterization.

ABSTRACT: Herein, we present a facile synthesis of three azide-functionalized fluorophores and their covalent attachment as triazoles in Huisgen-type cycloadditions with model alkynes. Besides two ortho- and para-bromo-substituted benzaldehydes, the azide functionalization of a fluorene-based structure will be presented. The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) of the so-synthesized azide-functionalized bromocarbaldehydes with terminal alkynes, exhibiting different degrees of steric demand, was performed in high efficiency. Finally, we investigated the photophysical properties of the azide-functionalized arenes and their covalently linked triazole derivatives to gain deeper insight towards the effect of these covalent linkers on the emission behavior.

SUBMITTER: Gobel D

PROVIDER: S-EPMC7372231 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Clickable azide-functionalized bromoarylaldehydes - synthesis and photophysical characterization.

Göbel Dominik D Friedrich Marius M Lork Enno E Nachtsheim Boris J BJ

Beilstein journal of organic chemistry 20200714

Herein, we present a facile synthesis of three azide-functionalized fluorophores and their covalent attachment as triazoles in Huisgen-type cycloadditions with model alkynes. Besides two <i>ortho</i>- and <i>para</i>-bromo-substituted benzaldehydes, the azide functionalization of a fluorene-based structure will be presented. The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) of the so-synthesized azide-functionalized bromocarbaldehydes with terminal alkynes, exhibiting different degrees ...[more]

PMID: 32733611

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